Novel anthelmintic and insecticidal compositions

Abstract

Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

What is claimed is:  
     
         1 . A compound of Formula I comprising:  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are selected from the group consisting of H, alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl, heteroaryl, substituted heteroaryl, hetroarylmethylene, and substituted hetroarylmethylene; or 
 R 1  and R 2 , along with the carbons to which they are attached, form a 5 to 7 membered substituted or unsubstituted carbocyclic or heterocyclic ring;  
 R 3  is alkyl of 1 to 4 carbons;  
 R 4 , and R 5  are independently alkyl, heteroalkyl, cycloalkyl, aryl, aralkyl, heteroaryl or heteroaralkyl;  
 R 4  and R 5  taken together may form a 4-7 membered substituted or unsubstituted carbocyclic ring;  
 R 6  and R 7  are independently H or alkyl of 1 to 3 carbons.  
 
     
     
         2 . A compound according to  claim 1  selected from the group consisting of: 
 ethyl 2-{[(4-phenylpiperidin-1-yl)acetyl]amino}-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 2-[(azetidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 4-(5-methylpyridin-2-yl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 5-ethyl-5-methyl-2-[(piperidin-1-ylacetyl)amino]-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylate;  
 ethyl 4-(2-furyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 6-benzyl-2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4-pyridin-4-ylthiophene-3-carboxylate;  
 ethyl 4-methyl-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 4-(4-bromophenyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 5-[(piperidin-1-ylacetyl)amino]-2,3′-bithiophene-4-carboxylate;  
 ethyl 5-[(piperidin-1-ylacetyl)amino]-3,3′-bithiophene-4-carboxylate;  
 isopropyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 Isopropyl 4-(3,4-dichlorophenyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4,5-dihydrothieno[2,3-b]thiophene-3-carboxylate;  
 ethyl 2-{[(4-hydroxypiperidin-1-yl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate; and  
 ethyl 2-{[(3-hydroxypiperidin-1-yl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate.  
 
     
     
         3 . A method for treating or preventing parasitic diseases in mammals comprising the step of administering to the mammal an effective amount of a compound of  claim 1 .  
     
     
         4 . A method for treating or preventing parasitic diseases in mammals according to  claim 3  wherein the compound is selected from the group consisting of: 
 ethyl 2-{[2-( 1-piperidinyl)acetyl]amino}-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 2-[(morpholin-4-ylacetyl)amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]thiophene-3-carboxylate;  
 ethyl 2-[(morpholin-4-ylacetyl)amino]-4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]thiophene-3-carboxylate;  
 ethyl 2-{[(4-phenylpiperidin-1-yl)acetyl]amino}-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 2-[(pyrrolidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 2-[(azepan-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 2-[(azetidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 2-[(pyrrolidin-1-ylacetyl)amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 2-[(azepan-1-ylacetyl)amino]-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate;  
 ethyl 5-chloro-4-phenyl-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 6-phenyl-2-[(piperidin-1-ylacetyl)amino]-4,5 ,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 6-tert-butyl-2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 2-[(2-piperidin-1-ylpropanoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 diethyl 2-[(piperidin-1-ylacetyl)amino]-4,7-dihydrothieno[2,3-c]pyridine-3,6(5H)-dicarboxylate;  
 ethyl 5-methyl-2-[(piperidin-1-ylacetyl)amino]-4,5 ,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 4-(5-methylpyridin-2-yl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 5-ethyl-5-methyl-2-[(piperidin-1-ylacetyl)amino]-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylate;  
 ethyl 4-(2-furyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 6-benzyl-2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4-pyridin-4-ylthiophene-3-carboxylate;  
 ethyl 4-methyl-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 methyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 propyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 ethyl 4-(4-bromophenyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 5-[(piperidin-1-ylacetyl)amino]-2,3′-bithiophene-4-carboxylate;  
 ethyl 5-[(piperidin-1-ylacetyl)amino]-3,3′-bithiophene-4-carboxylate;  
 Isopropyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate;  
 isopropyl 4-(3,4-dichlorophenyl)-2-[(piperidin-1-ylacetyl)amino]thiophene-3-carboxylate;  
 ethyl 2-[(piperidin-1-ylacetyl)amino]-4,5-dihydrothieno[2,3-b]thiophene-3-carboxylate;  
 ethyl 2-{[(4-hydroxypiperidin-1-yl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate; and  
 ethyl 2-{[(3-hydroxypiperidin-1-yl)acetyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate.  
 
     
     
         5 . A composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier.  
     
     
         6 . A composition comprising a compound of  claim 3  and a pharmaceutically acceptable carrier.  
     
     
         7 . The use of a compound of  claim 1  to prepare a medicament for treating or preventing parasitic diseases in mammals.  
     
     
         8 . The use of a compound of  claim 3  to prepare a medicament for treating or preventing parasitic diseases in mammals.